CN1934116B - 用作抗心律失常剂的三环苯并吡喃化合物 - Google Patents
用作抗心律失常剂的三环苯并吡喃化合物 Download PDFInfo
- Publication number
- CN1934116B CN1934116B CN2005800090295A CN200580009029A CN1934116B CN 1934116 B CN1934116 B CN 1934116B CN 2005800090295 A CN2005800090295 A CN 2005800090295A CN 200580009029 A CN200580009029 A CN 200580009029A CN 1934116 B CN1934116 B CN 1934116B
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- China
- Prior art keywords
- amino
- pyrans
- dihydro
- quinoline
- alcohol
- Prior art date
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- -1 benzopyran compound Chemical class 0.000 title claims description 742
- 239000003416 antiarrhythmic agent Substances 0.000 title abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 104
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 547
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 179
- 125000005843 halogen group Chemical group 0.000 claims description 159
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 104
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 102
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical class C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 29
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- OZMHIFNNCZPJFS-UHFFFAOYSA-N quinoline-7-carbonitrile Chemical compound C1=CC=NC2=CC(C#N)=CC=C21 OZMHIFNNCZPJFS-UHFFFAOYSA-N 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
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- WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
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- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 131
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 53
- 229910052760 oxygen Inorganic materials 0.000 abstract description 40
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 abstract description 6
- 125000003277 amino group Chemical group 0.000 abstract description 3
- 125000004429 atom Chemical group 0.000 abstract description 3
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- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
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- 238000006243 chemical reaction Methods 0.000 description 119
- 235000002639 sodium chloride Nutrition 0.000 description 94
- 239000007864 aqueous solution Substances 0.000 description 89
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 85
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 70
- 125000003545 alkoxy group Chemical group 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 60
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 60
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- 235000019253 formic acid Nutrition 0.000 description 54
- 238000000034 method Methods 0.000 description 54
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 48
- 238000005406 washing Methods 0.000 description 46
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- 238000001035 drying Methods 0.000 description 43
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- 239000001301 oxygen Substances 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 34
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- 239000012074 organic phase Substances 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 31
- 239000007787 solid Substances 0.000 description 31
- 238000010025 steaming Methods 0.000 description 31
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- 238000003756 stirring Methods 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
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- 238000002425 crystallisation Methods 0.000 description 19
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 210000003516 pericardium Anatomy 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 description 1
- ROIMLVZGQKCUCQ-UHFFFAOYSA-N phosphane propane Chemical compound CCC.P ROIMLVZGQKCUCQ-UHFFFAOYSA-N 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- NNOBHPBYUHDMQF-UHFFFAOYSA-N propylphosphine Chemical class CCCP NNOBHPBYUHDMQF-UHFFFAOYSA-N 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 235000019721 spearmint oil Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000005458 thianyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D515/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D515/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Dental Preparations (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP084605/2004 | 2004-03-23 | ||
| JP2004084605 | 2004-03-23 | ||
| PCT/JP2005/006004 WO2005090357A1 (en) | 2004-03-23 | 2005-03-23 | Tricyclic benzopyran compound as anti-arrhythmic agents |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008101707921A Division CN101429200B (zh) | 2004-03-23 | 2005-03-23 | 用作抗心律失常剂的三环苯并吡喃化合物 |
| CN2011100751168A Division CN102190661B (zh) | 2004-03-23 | 2005-03-23 | 用作抗心律失常剂的三环苯并吡喃化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1934116A CN1934116A (zh) | 2007-03-21 |
| CN1934116B true CN1934116B (zh) | 2012-10-10 |
Family
ID=34962589
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008101707921A Expired - Fee Related CN101429200B (zh) | 2004-03-23 | 2005-03-23 | 用作抗心律失常剂的三环苯并吡喃化合物 |
| CN2011100751168A Expired - Fee Related CN102190661B (zh) | 2004-03-23 | 2005-03-23 | 用作抗心律失常剂的三环苯并吡喃化合物 |
| CN2005800090295A Active CN1934116B (zh) | 2004-03-23 | 2005-03-23 | 用作抗心律失常剂的三环苯并吡喃化合物 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008101707921A Expired - Fee Related CN101429200B (zh) | 2004-03-23 | 2005-03-23 | 用作抗心律失常剂的三环苯并吡喃化合物 |
| CN2011100751168A Expired - Fee Related CN102190661B (zh) | 2004-03-23 | 2005-03-23 | 用作抗心律失常剂的三环苯并吡喃化合物 |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US7652008B2 (ko) |
| EP (1) | EP1732929B1 (ko) |
| JP (1) | JP4840594B2 (ko) |
| KR (2) | KR101085979B1 (ko) |
| CN (3) | CN101429200B (ko) |
| AT (1) | ATE485299T1 (ko) |
| AU (2) | AU2005223612B2 (ko) |
| BR (1) | BRPI0508768A (ko) |
| CA (1) | CA2558139C (ko) |
| CY (1) | CY1111250T1 (ko) |
| CZ (1) | CZ2006598A3 (ko) |
| DE (1) | DE602005024245D1 (ko) |
| DK (1) | DK1732929T3 (ko) |
| EG (1) | EG27163A (ko) |
| ES (1) | ES2353021T3 (ko) |
| HK (1) | HK1099299A1 (ko) |
| HR (1) | HRP20110005T1 (ko) |
| IL (1) | IL177950A (ko) |
| MX (1) | MXPA06010880A (ko) |
| NO (1) | NO339495B1 (ko) |
| NZ (2) | NZ585606A (ko) |
| PL (1) | PL1732929T3 (ko) |
| PT (1) | PT1732929E (ko) |
| RS (1) | RS51742B (ko) |
| RU (1) | RU2380370C2 (ko) |
| SI (1) | SI1732929T1 (ko) |
| SK (1) | SK287994B6 (ko) |
| TW (1) | TWI352704B (ko) |
| UA (1) | UA91189C2 (ko) |
| WO (1) | WO2005090357A1 (ko) |
| ZA (1) | ZA200607388B (ko) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA200607388B (en) * | 2004-03-23 | 2008-07-30 | Nissan Chemical Ind Ltd | Tricyclic benzopyran compound as anti-arrhythmic agents |
| US8394974B2 (en) | 2006-03-10 | 2013-03-12 | Nissan Chemical Industries, Ltd. | Process for producing optically active chromene oxide compound |
| JPWO2010018867A1 (ja) * | 2008-08-14 | 2012-01-26 | 日産化学工業株式会社 | ジ置換ベンゾピラン化合物 |
| RU2523279C2 (ru) * | 2009-04-30 | 2014-07-20 | Ниссан Кемикал Индастриз, Лтд. | Новая кристаллическая форма соединения трициклического бензопирана и способ его производства |
| NZ597107A (en) | 2009-06-25 | 2013-12-20 | Alkermes Pharma Ireland Ltd | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| JP6202280B2 (ja) * | 2012-09-27 | 2017-09-27 | 日産化学工業株式会社 | 含窒素複素環ｎ−オキシド化合物の製造方法 |
| US9464095B2 (en) | 2012-09-27 | 2016-10-11 | Nissan Chemical Industries, Ltd. | Production method of high-purity nitrogen-containing heterocyclic compound |
| CN105377826A (zh) * | 2013-07-25 | 2016-03-02 | 日产化学工业株式会社 | 杂环化合物的制造方法 |
| KR102009756B1 (ko) | 2017-01-06 | 2019-08-12 | 고려대학교 세종산학협력단 | 신규한 퀴놀리논 유도체 및 이를 유효성분으로 포함하는 천식 또는 아토피 등의 알러지성 질환의 예방 또는 치료용 약학 조성물 |
| WO2019173230A1 (en) | 2018-03-05 | 2019-09-12 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
| CN108727261B (zh) * | 2018-06-21 | 2021-09-24 | 济南大学 | 一种硝基取代喹那啶的制备方法 |
| CN113543849A (zh) * | 2018-12-28 | 2021-10-22 | 国立大学法人大阪大学 | 遗传性缓慢性心律失常治疗药 |
| RU2754610C1 (ru) * | 2020-04-14 | 2021-09-03 | Георгий Викторович ТЕЦ | Препарат для лечения заболеваний, вызванных бактериями |
| CN115916201A (zh) * | 2020-06-26 | 2023-04-04 | 国立大学法人大阪大学 | 药剂诱发性心动过缓及心动过缓性心律失常治疗药 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZM7682A1 (en) | 1981-09-25 | 1983-05-23 | Beecham Group Plc | Active compounds |
| JPS5867683U (ja) | 1981-10-28 | 1983-05-09 | 株式会社ナムコ | 歩行ロボツト |
| JPH0699439B2 (ja) * | 1988-02-03 | 1994-12-07 | 日産化学工業株式会社 | ピラノベンゾオキサジアゾール誘導体 |
| JP2658198B2 (ja) | 1988-06-23 | 1997-09-30 | 日産化学工業株式会社 | ピラノベンゾトリアゾール誘導体 |
| JP2876712B2 (ja) * | 1989-07-17 | 1999-03-31 | 日産化学工業株式会社 | 光学活性ピラノベンゾオキサジアゾール誘導体 |
| US5097037A (en) | 1989-07-17 | 1992-03-17 | Nissan Chemical Industries, Ltd. | Process for the optical resolution of pyranobenzoxadiazole compounds |
| US5164509A (en) * | 1990-11-26 | 1992-11-17 | E. R. Squibb & Sons, Inc. | Benzodiazolo analogs |
| HUT73971A (en) * | 1993-04-02 | 1996-10-28 | Nissan Chemical Ind Ltd | Heart failure remedy |
| JPH07300414A (ja) * | 1993-04-02 | 1995-11-14 | Nissan Chem Ind Ltd | 心不全治療薬 |
| JP2734457B2 (ja) | 1994-02-23 | 1998-03-30 | 日産化学工業株式会社 | 不斉エポキシ化反応 |
| DE69518322T2 (de) * | 1994-06-10 | 2001-02-15 | Smithkline Beecham P.L.C., Brentford | C-4 amid substituierte verbindungen und deren verwendung als therapeutische mittel |
| HRP970255B1 (en) * | 1996-05-15 | 2003-10-31 | Hoechst Ag | Sulfonamido substituted chromane derivatives, method for their preparation, their use as medicaments or diagnostic agents as well as medicaments containing them |
| US6486178B1 (en) | 1998-06-03 | 2002-11-26 | Nissan Chemical Industries, Ltd. | Indane derivatives |
| AU5444499A (en) | 1998-09-01 | 2000-03-21 | Nissan Chemical Industries Ltd. | Benzoxazine derivatives |
| AU2830800A (en) | 1999-03-25 | 2000-10-16 | Nissan Chemical Industries Ltd. | Chroman derivatives |
| IL147968A0 (en) | 1999-09-17 | 2002-09-12 | Nissan Chemical Ind Ltd | Benzopyran derivative |
| US6555574B1 (en) | 1999-09-24 | 2003-04-29 | Nissan Chemical Industries, Ltd. | 4-oxybenzopyran derivative |
| WO2001025224A1 (en) | 1999-10-05 | 2001-04-12 | Nissan Chemical Industries, Ltd. | 4-oxybenzopyran derivative |
| TW589305B (en) | 2001-02-14 | 2004-06-01 | Nissan Chemical Ind Ltd | 4-aminobenzopyran derivatives |
| IL159218A0 (en) | 2001-06-25 | 2004-06-01 | Nissan Chemical Ind Ltd | Substituted benzopyran derivatives against arrhythmia |
| WO2003014113A1 (en) | 2001-08-06 | 2003-02-20 | Glenmark Pharmaceuticals Limited | Novel benzopyran compounds and process for their preparation and use |
| ZA200607388B (en) * | 2004-03-23 | 2008-07-30 | Nissan Chemical Ind Ltd | Tricyclic benzopyran compound as anti-arrhythmic agents |
-
2005
- 2005-03-23 ZA ZA200607388A patent/ZA200607388B/en unknown
- 2005-03-23 RU RU2006137284/04A patent/RU2380370C2/ru not_active IP Right Cessation
- 2005-03-23 BR BRPI0508768-6A patent/BRPI0508768A/pt not_active Application Discontinuation
- 2005-03-23 US US10/590,975 patent/US7652008B2/en active Active
- 2005-03-23 KR KR1020107027058A patent/KR101085979B1/ko active IP Right Grant
- 2005-03-23 PL PL05727581T patent/PL1732929T3/pl unknown
- 2005-03-23 TW TW094108962A patent/TWI352704B/zh active
- 2005-03-23 SK SK5079-2006A patent/SK287994B6/sk not_active IP Right Cessation
- 2005-03-23 NZ NZ585606A patent/NZ585606A/en unknown
- 2005-03-23 AU AU2005223612A patent/AU2005223612B2/en not_active Ceased
- 2005-03-23 EP EP05727581A patent/EP1732929B1/en active Active
- 2005-03-23 DE DE602005024245T patent/DE602005024245D1/de active Active
- 2005-03-23 CA CA2558139A patent/CA2558139C/en not_active Expired - Fee Related
- 2005-03-23 RS RS20110028A patent/RS51742B/en unknown
- 2005-03-23 CN CN2008101707921A patent/CN101429200B/zh not_active Expired - Fee Related
- 2005-03-23 NZ NZ549570A patent/NZ549570A/en unknown
- 2005-03-23 CN CN2011100751168A patent/CN102190661B/zh not_active Expired - Fee Related
- 2005-03-23 MX MXPA06010880A patent/MXPA06010880A/es active IP Right Grant
- 2005-03-23 PT PT05727581T patent/PT1732929E/pt unknown
- 2005-03-23 CZ CZ20060598A patent/CZ2006598A3/cs unknown
- 2005-03-23 SI SI200531171T patent/SI1732929T1/sl unknown
- 2005-03-23 AT AT05727581T patent/ATE485299T1/de active
- 2005-03-23 KR KR1020067021988A patent/KR101019402B1/ko active IP Right Grant
- 2005-03-23 WO PCT/JP2005/006004 patent/WO2005090357A1/en active Application Filing
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Non-Patent Citations (4)
| Title |
|---|
| Medicinal Chemisty Letters》.1997,第7卷(第12期),1573-157. * |
| Wai N. Chan等.CONFORMATIONAL PREFERENCE OF THE 6-ACETYL GROUP IN NOVEL ANTICONVULSANT trans 4S-BENZAMIDO-BENZO[b]PYRAN-3R-OLS.《Bioorganic & Medicinal Chemisty Letters》.1997,第7卷(第12期),1573-157. |
| Wai N. Chan等.CONFORMATIONAL PREFERENCE OF THE 6-ACETYL GROUP IN NOVEL ANTICONVULSANT trans 4S-BENZAMIDO-BENZO[b]PYRAN-3R-OLS.《Bioorganic & * |
| Yoshiko Kuwahara.国际初审报告.《PCT/IB/373》.2006, * |
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